


all dressed up and naked

by cathect



Category: The Umbrella Academy (TV)
Genre: Anal Sex, Established Relationship, Feminization, Five In A Skirt, Five's Body Is Sixteen, M/M, Plot What Plot/Porn Without Plot, Porn with Feelings
Language: English
Status: Completed
Published: 2019-03-18
Updated: 2019-03-18
Packaged: 2019-11-23 22:27:19
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,500
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18157847
Author URL: https://archiveofourown.org/users/cathect/pseuds/cathect
Summary: -The skirt hanging off of it is pleated and pale pink, with two white stripes near the hem—like a cheerleader might wear, Diego thinks wildly— and Five looks almost awed. Diego doesn’t want to assume anything by an expression alone, but he can’t quite help it.Before he can stop himself, the words are tumbling out. “That would look good on you.”-or, the one where diego fucks five while he's wearing a skirt.





	all dressed up and naked

**Author's Note:**

> just like the tags say, five's body is sixteen, but his consciousness would be like sixty-one so don't @ me.
> 
> big thank you to erin for beta'ing, as always!

“This is stupid,” Five says. “The clothes I have now are just fine.”

Diego snorts. “No, they’re not,” he replies easily. Even in a new timeline, nearly six months after saving the world, the only things in Five’s closet are academy uniforms. “You can’t just keep wearing the same outfit every day, Five.”

“ _You_ do it just fine.” The barest hint of venom drips from his voice and, okay, Diego is going to give him that one— partly because Diego would be pissy, too, after spending an hour trying on clothes he didn’t want, but mostly because it’s true. Even if he’d never admit it out loud. It’s rare for him to be seen in anything besides his normal black-on-black ensemble.

When Diego looks over, Five is glaring at the clothes in his arms like he could light them on fire with enough willpower. It’s not even that many things, just the basics, but the process of finding the right sizes and styles had been a long one. They spent nearly three years in the past, trying to fix the mistakes that led to the apocalypse, and Five is the only one whose aging really affected him. He’s taller at sixteen than he was at thirteen; it’s not by much, but it’s enough that his shirts are riding up and his shorts are just small enough to be a problem.

Five sighs. “I’m sorry,” he says. “It’s just annoying, doing all this again.”

“I know,” Diego replies, even though he doesn’t. He can’t imagine having to go through puberty twice. All things considered, he thinks Five is handling it remarkably well.

Five’s free hand hangs at his side, and Diego’s fingers twitch with the urge to reach out and link with his brother’s. He can’t. Not here, not in public, no matter how much he wishes he could. To the prying eyes of any stranger, Five is a teenager, and Diego is way too old to be holding his hand. Diego _knows_ how it looks— he’s suffered enough nights with no sleep over the moral dilemma of being with someone in a sixteen-year-old’s body— so he shoves his hand into his pocket instead.

Diego’s so caught up in his musings that he gets a full ten feet before he realizes that Five isn’t next to him anymore.

“Five?” He asks. He turns as he speaks and sees Five standing in front of a few racks of clothes. Diego walks to him slowly, glances up at the sign overhead that reads _women’s_. “Five?”

“Sorry, I…” Five clears his throat when his voice catches, but he doesn’t look at Diego. His fingers dance over the hangers in front of him for a brief moment before he plucks one off the rack and holds it up. 

The skirt hanging off of it is pleated and pale pink, with two white stripes near the hem— _like a cheerleader might wear_ , Diego thinks wildly— and Five looks almost awed. Diego doesn’t want to assume anything by an expression alone, but he can’t quite help it. 

Before he can stop himself, the words are tumbling out. “That would look good on you.”

Five looks up and, for a terrifying second, Diego thinks he’s read this wrong. Maybe Five was just looking and Diego’s the asshole who’s suppressing a boner picturing his brother in a skirt. He readies himself for a smack upside the head and a lecture that’ll last the whole ride home, but it doesn’t come. Instead, Five’s cheeks turn as pink as the skirt and his eyes are wide when he finally meets Diego’s gaze. 

“Really?” He asks. The arm laden with other clothes is lowering slowly, like without Five’s full attention he can’t quite keep it up. “You think so?”

Diego swallows around the sudden lump in his throat and nods. “Yeah,” he says truthfully. As Five’s arm continues in its descent, Diego reaches out to lighten the load. “Here, let me.”

“Thanks,” Five says as he hands over the clothes. All except the skirt, which he takes with him to a nearby mirror. Diego watches, fascinated, as Five holds it up to his body and studies his reflection, turns a little each way and tilts his head.

Diego takes a step closer. “You should get it,” he says softly. Five meets his eyes in the mirror; his face is cautious, like he’s waiting for the other shoe to drop, for Diego to turn the whole thing into a joke. “If you want to, I mean,” Diego amends. He doesn’t want to push Five to do something he isn’t ready to do just because he likes the idea.

“Really?” Five asks again. It’s like he can’t help it, and Diego doesn’t fault him for it. It’s not weird or anything— after some of the things they’ve seen Klaus in, it would be a feat for Five to find something to wear that’s _weird_ — but it is different, and God knows they’ve had enough different in their lives already. 

Still, the look in Five’s eyes is more hopeful than afraid. Diego lays a gentle hand on his shoulder and says, “Absolutely.” 

“Okay.” Five holds the hanger out to Diego slowly, and Diego takes it from him, laying the skirt over his arm with the other clothes. Five looks at it for another long moment before he nods. “Okay,” he says again, and that’s that.

 

The drive back to the mansion is quiet at first, save for the sound of the shopping bags rustling in the back seat, moving around a little with each turn they take. Five is looking out the window, silent and contemplative. Diego wants to give him as much space to think as he can when they’re confined to the same car, so he keeps his eyes on the road and his thoughts to himself.

It’s only when they’re almost home that Five reaches over and laces his fingers with Diego’s. “Thanks for earlier,” he says. His voice isn’t nearly as soft as it was in the store, but it still hasn’t returned to its normal pitch and attitude. 

“Yeah, of course.” Diego squeezes his hand gently. “I meant what I said. It’ll look good on you.” 

“I don’t...” Five audibly swallows. “I don’t think I want to wear it— out, or anything.” He doesn’t sound nervous, exactly. It’s more like he’s processing his own thoughts out loud.

“No?” Diego asks.

Five shakes his head, something Diego sees out of the corner of his eye. “No, just.” Five strokes his thumb over the back of Diego’s hand absentmindedly. “Just for you.”

Diego’s chest tightens at the thought that this is something Five wants to share with him, with _only_ him. He lifts their hands and bring’s Five’s to his lips. He kisses Five’s knuckles and hopes that it says everything he can’t with his tongue tied up in knots. If the smile on Five’s face when Diego looks to the passenger seat is any indication, it does.

-

They don’t talk about it for over a week.

Five doesn’t bring it up, so Diego doesn’t either, even though it’s all he thinks about. He wonders where Five put it. He can picture it, wrapped up in one of the shopping bags, shoved to the back corner of Five’s dresser. Or maybe Five decided to hang it up with all his other clothes, and he looks at it every time he gets dressed. Diego wonders if he’s tried it on yet.

It’s one of the hardest things Diego’s ever done, resisting the urge to ask Five about it every time he sees him. And Five does nothing to limit their contact or avoid Diego in any way; they still eat together and hang out with the others and sleep in the same bed most nights. It’s clear that Five is perfectly fine with having Diego burn holes into the side of his face with his gaze any time they’re in the same room.

Above everything else, though, Diego’s starting to get worried. He’s never really known Five to panic but, then again, this is uncharted territory. Part of him wants to sit Five down and reassure him, tell him that if he’s not ready or if he’s changed his mind it’s _okay_. The rest of him knows that he shouldn’t. This is Five’s thing and, just like in the store, Diego doesn’t want to push him— in either direction. 

So, he waits.

And waits.

And _waits_.

He forcibly holds his tongue for so long that he feels like he could cry in relief the night he comes into his room to find Five waiting for him, all dressed up in nothing but that pretty pink skirt.

“Shit,” Diego breathes. Five smirks where he’s perched on the edge of Diego’s bed. “Shit,” Diego says again. It’s all he can manage with his brain short-circuiting.

Five laughs as he stands up. “So you said.” He doesn’t walk closer, and Diego is grateful for the opportunity to take in all of his appearance.  
  
The skirt looks just as good as Diego knew it would. _Better_ , even. It’s a little big, sitting precariously at his waist, but the pleats fall just where they should on his hips and the hem brushes his mid-thigh. His long legs somehow look even _longer_ and Diego nearly chokes on his next inhale when he processes the fact that they’re smooth and hairless. It wasn’t some random burst of confidence that led to Five coming to his room tonight. He’s been planning this. He _prepared_ for this.

“As much as I’m flattered by your silence,” Five says, shifting his weight from foot to foot, “I’d really appreciate it if you said something.” 

“Sorry,” Diego says immediately. “You just look— I mean— _Jesus_ , Five.”

Five bites his lip on a smile that looks almost nervous. “Do—?” His fingers flex at his sides. “Do I look pretty?”

Diego is across the room in a flash, hands finding Five’s hips and squeezing. The tension in Five’s body seems to dissipate, at least minutely, from the contact, and he melts into Diego’s touch. Diego kisses him sweetly, tastes the worry on his tongue. He pulls back with a smile.

“You look so pretty, baby,” Diego murmurs. He tugs Five closer by his hips, suddenly jealous of the space between them. The blush that was high on Five’s cheeks bleeds down to his chest and Diego follows it with his eyes for a moment before bringing them back to Five’s face. “Do you like it?”

Five nods. “I like the way I feel in it,” he says quietly. “And I like the way you’re looking at me.”

“I always look at you like this,” Diego counters, thumbs rubbing gentle circles into Five’s hips.

“No, you don’t.” Five leans up on his toes to kiss Diego and then he’s falling back onto the bed. “Now, get over here. I’ve been waiting for, like, a fucking hour.” 

Diego groans, thinking about Five lying in wait in his bed while Diego was downstairs shooting the shit with Klaus and Ben. He peels off his clothes so fast he nearly makes himself dizzy, shirt and sweatpants and boxers all ending up in a pile on the floor that Five will bitch about later. He climbs up onto the bed and kneels between Five’s thighs. Diego’s fingers trail up the smooth skin of Five’s calves.

A shiver runs through Five’s body and his voice shakes a little when he speaks. “I asked Allison for help,” he offers without prompting. Diego’s eyes immediately flick up to meet Five’s. “Didn’t exactly have Dad around to teach me how to shave during the apocalypse, you know?”

Diego nods. He wants Five to know he’s listening, but doesn’t want to interrupt.

“She was— surprisingly helpful,” Five continues. He blabs a little when he’s nervous, Diego’s noticed. It would be worrisome right now if his cock wasn’t hard and tenting the front of the skirt. “She didn’t make me feel weird for asking, or anything.”

Diego hums in response, figuring that Five isn’t looking for an especially eloquent reply, and Five’s explanation stops there. Diego strokes his thumb over Five’s knee then continues his ascent, dancing his fingers across Five’s inner thighs before spreading his legs apart gently. The skirt falls from around his thighs and pools at his waist. 

Diego _tsks_ at the sight of Five’s black cotton briefs. “Should’ve gotten you some panties or something,” he remarks softly, unable to keep the words behind his teeth once the thought hits him. “Would’ve really tied the whole look together.”

Five gasps and squirms underneath him, and Diego grins.

“Oh?” He teases, moving up Five’s body until he can hold himself over his brother and bring them eye-to-eye. “Someone likes the sound of that, huh?”

“Shut up,” Five admonishes. Diego can tell he’s trying to frown, but he’s really only succeeding in looking endlessly fond. 

“Something made of lace, maybe,” Diego continues, almost talking more to himself than Five. His thoughts have taken flight like a fucking rocket, soaring through the possibilities. It’s all he can do to get a coherent sentence out— the first one that comes to mind. “You’d look so _pretty_ in lace, baby girl.”

As soon as the words leave his mouth, Diego wants to pluck them from the air between them and shove them back down his throat. Here Five is, already nervous and vulnerable, and Diego had to go and say _that_. Five doesn’t say anything, but Diego can feel his eyes on him.

“I’m sorry,” Diego rushes. He focuses on the curve of Five’s jaw; Diego knows all too well the unimpressed glare he’ll be met with if he looks at his brother’s face. “I just got caught up, and—?”

“Shut up,” Five says again, and yanks Diego into a kiss. It’s messy, all clacking teeth and no finesse. Diego pulls back after a minute, breathless, to find Five looking up at him through his eyelashes with cherry-red cheeks. “You don’t have to be sorry, I— I liked it.” 

“Yeah?” Diego asks gently, just to be safe. 

“Yeah,” Five breathes. Then, his eyebrows furrow and he _does_ pin Diego with a glare. “But, if you don’t get this fucking show on the road, sorry’s not going to cut it.”

Diego swallows the natural instinct to laugh and kisses Five again, slow and dirty and deep. Five moans when Diego sucks on his tongue, bucks his hips up and shudders as he grinds his cock against Diego’s thigh. Diego breaks the kiss to trail his lips down Five’s neck, nipping at the skin as he goes. He stops when he reaches the center of Five’s chest and looks up at him. 

“Want my mouth on your tits, baby?” He tries. Five whines pitifully and arches his back, puts himself on display and, really, how is Diego supposed to say no to that? 

He turns his head and takes one of Five’s nipples into his mouth. Five gasps when Diego bites down, and then whimpers when he soothes the sting with the flat of his tongue. His fingers bury themselves in Diego’s short hair, nails digging into his scalp when Diego moves to his other nipple and gives it the same treatment.

“Diego,” Five moans. He grabs at one of Diego’s hands where it’s cradling his ribs and drags it down between his legs, presses it against the growing damp patch on his briefs. “Fucking _touch_ me, you asshole,” he begs, voice practically a sigh. 

Diego snorts but obliges. He reaches into Five’s underwear as he sucks a hickey into his chest. He wraps his hand around Five’s cock, fingers sticky with precome, and listens to Five’s shaky inhale. “You’re so wet, baby girl,” Diego murmurs, kissing Five’s stomach. 

Five mewls like a goddamn kitten and bucks his hips up into Diego’s fist. Diego strokes him at an agonizing pace just to watch Five’s face contort in equal parts pleasure and frustration. What can Diego say? He wants to take his time. He’d take all night, if his own cock wasn’t heavy and aching. Five is almost never sweet and needy like this; Diego relishes it while he can.

After a minute, though, it’s impossible to keep up the torturous pace. He lets go of Five’s cock, smirking a little when he whines with the loss. “Wanna fuck you,” Diego says, drawing Five’s briefs down his thighs and tossing them onto the floor. He pointedly leaves the skirt in place.

“ _Please_.” Five bites at his lip. “I, umm. I got myself ready for you.”

Diego’s cock jumps and he groans. “Yeah?” Five nods his head so hard that Diego’s half-worried it’ll roll off his shoulders. “Just that impatient, hmm?”

“Fuck off,” Five snaps, but he looks a little sheepish. Diego grins and falls forward to kiss him, his lips and his cheeks and his chin and his nose. Five laughs under the onslaught of attention and Diego can’t help but stare. He needs to be inside Five so badly. 

Diego flings a hand out to dig in the drawer of his nightstand for the bottle of lube he keeps stashed in it and, sure enough, it’s significantly emptier than Diego remembers. Five must have been thorough. Diego taught him well. He squeezes a dollop into his hand and spreads it over his cock as Five hooks his legs over Diego’s hips.

“Diego,” Five whines, drawing out the last syllable impatiently.

Diego nods. “I know, baby,” he says. “I’m going.” He guides his cock into Five with one hand and sinks in dizzyingly easy, down to the hilt. They let out near-identical moans as he bottoms out, and Five throws an arm around Diego’s shoulders to pull him closer.

Diego wastes no time before starting up a brutal pace; neither of them is going to last very long, Diego knows. Not after all the anticipation and teasing, not with the way Five’s cries come out so broken as Diego fucks him. Five looks like a work of art, hair falling onto his forehead and sticking with sweat, cock leaking steadily onto the fabric of the skirt. Long, dark eyelashes and kiss-bitten lips. He looks so beautiful it should be illegal, and Diego tells him as much.

“Love watching you take my cock.” Diego speaks against the hinge of Five’s jaw and nips at the sensitive skin there as he snaps his hips forward, aiming directly for Five’s prostate with every thrust. “It’s like you were made for it.” 

Five keens and hauls Diego in for a kiss. “Please,” he says when it breaks. “M’so close, Diego.” 

“Touch yourself, sweetheart,” Diego urges. “Wanna watch you make yourself come.” Five nods and reaches between their bodies to get a hand on his cock. Diego hums approvingly as Five starts to stroke himself. “There’s a good girl.” 

Five comes suddenly with a shout, spilling over his fist and onto the skirt. He writhes on the bed underneath Diego, still working his cock with one hand and fisting the other in the bed sheets. His noises are endless and _loud_ , filling up all the empty space in the room until Diego thinks he might drown in them. He buries his face in Five’s neck as he fucks into him too hard, without any semblance of rhythm.

“Come on,” Five says in his ear, clenching down on Diego’s cock. His voice sounds absolutely ruined. “Come in me, Diego, come on.” 

Diego groans and nods and then he’s coming so hard that stars dance across his eyelids when he squeezes them shut. His thrusts turn sharp and shallow as he chases his orgasm, little sparks of pleasure skating across his nerves and lighting them on fire.

It takes nearly all of Diego’s concentration not to collapse onto Five as he comes down, but he manages. He kisses Five gently, licks into his mouth lazily and swallows his brother’s soft noise of protest as Diego pulls out. Time seems to slow to a stop around them, and Diego pulls back to make a joke about it, only to find Five frowning and looking down between their bodies.

“What?” Diego asks, following his line of sight. Five is holding up the hem of the skirt, examining the drying come on the fabric. Diego laughs and shakes his head. “Don’t worry, babe. We’ll get you another skirt.”

Five’s face lights up, but he visibly tries to tone down his excitement. “Yeah?” He asks. Diego nods and Five hesitates before he continues. “Maybe some— some panties, too?”

“Anything you want,” Diego promises. “We’ll make a whole day of it.” Diego’s not actually sure he could handle an entire day of buying Five pretty things, but he keeps that to himself.

“It’s a date,” Five says with a smile brighter than the sun, one that Diego can’t help but return. 

Diego kisses Five, nips at his bottom lip playfully. “It’s a date,” he agrees.

**Author's Note:**

> i do not accept constructive criticism.
> 
> follow me on tumblr @devilstrip !


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